(2R,3R,4S,5R)?2?(4?aminopyrrolo[1,2?f][1,2,4]triazin?7?yl)?3,4?dihydroxy?5?(hydroxymethyl)tetrahydrofuran?2?carbonitrile

Base Information

• Chemical Name: (2R,3R,4S,5R)?2?(4?aminopyrrolo[1,2?f][1,2,4]triazin?7?yl)?3,4?dihydroxy?5?(hydroxymethyl)tetrahydrofuran?2?carbonitrile
• CAS No.: 1191237-69-0
• Molecular Formula: C₁₂H₁₃N₅O₄
• Molecular Weight: 291.266
• Mol file: 1191237-69-0.mol

Synonyms:(2R,3R,4S,5R)?2?(4?aminopyrrolo[1,2?f][1,2,4]triazin?7?yl)?3,4?dihydroxy?5?(hydroxymethyl)tetrahydrofuran?2?carbonitrile

Chemical Property of (2R,3R,4S,5R)?2?(4?aminopyrrolo[1,2?f][1,2,4]triazin?7?yl)?3,4?dihydroxy?5?(hydroxymethyl)tetrahydrofuran?2?carbonitrile

Chemical Property:

• Melting Point: > 233° C (dec.)
• Density: 1.84±0.1 g/cm3(Predicted)

Purity/Quality:

99% ^*data from raw suppliers

GS441524 ≥98%(HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: GS-441524 is a nucleoside analogue that terminates the RNA chain of viral RNA-dependent RNA polymerase. GS-441524 was developed by Gilead Sciences, Inc as part of their research into human RNA virus disease such as Ebola. GS-441524 is a small molecule that exhibits potent antiviral activity against a number of RNA viruses, including the zoonotic severe acute respiratory syndrome (SARS) coronavirus ( Cho et al., 2012). A phosphoramidate prodrug of GS-441524 (GS-5734) has been previously shown to inhibit the replication of several taxonomically diverse RNA viruses such as Middle East respiratory syndrome virus, Ebola virus, Lassa fever virus, Junin virus and respiratory syncytial virus, while having low cytotoxicity in a wide-range of cell lines ( Sheahan et al., 2017 ). GS-5734 has also been shown to protect rhesus monkeys from experimental Ebola virus infection ( Warren et al., 2016 ). GS-441524 is the active prodrug of the broad-spectrum antiviral Remdesivir. GS-441524 is an adenosine nucleotide analog in viral RNA production. It is a nucleotide analog inhibitor of RNA-dependent RNA polymerases (RdRps). The compound interferes with the action of viral RNA polymerase and evades proofreading by viral exoribonuclease (ExoN), causing a decrease in viral RNA production (RNA synthesis arrest), either by terminating RNA chains or causing mutations. It inhibits MERS-CoV or SARS-CoV-infected HAE cultures (EC50=74nM and 69nM) and murine hepatitis virus (MHV) (EC50=30nM). In vivo, remdesivir (25 and 50 mg/kg) reduces lung viral titers and prevents weight loss in a mouse model of SARS-CoV infection. Remdesivir is used as a treatment for Ebola virus disease and Marburg virus infections and other single stranded RNA viruses such as respiratory syncytial virus, Junin virus, Lassa fever virus, Nipah virus, Hendra virus and the coronaviruses (including MERS and SARS viruses). Remdesivir is effective in the control of 2019-nCoV (COVID-19) infection in vitro. It now also has been studied as potential treatment of SARS-CoV-2 infections.
• Uses: GS-441524 is originally identified as an active metabolite of Remdesivir that is an antiviral drug, a novel nucleotide analog prodrug.

Technology Process of (2R,3R,4S,5R)?2?(4?aminopyrrolo[1,2?f][1,2,4]triazin?7?yl)?3,4?dihydroxy?5?(hydroxymethyl)tetrahydrofuran?2?carbonitrile

There total 36 articles about (2R,3R,4S,5R)?2?(4?aminopyrrolo[1,2?f][1,2,4]triazin?7?yl)?3,4?dihydroxy?5?(hydroxymethyl)tetrahydrofuran?2?carbonitrile which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

(2R,3R,4R,5R)‐2‐{4‐aminopyrrolo[2,1‐f][1,2,4]triazin‐7‐yl}‐3,4‐bis(benzyloxy)‐5‐[(benzyloxy)methyl]tetrahydrofuran‐2‐carbonitrile (1355357-49-1) → (2R,3R,4S,5R)?2?(4?aminopyrrolo[1,2?f][1,2,4]triazin?7?yl)?3,4?dihydroxy?5?(hydroxymethyl)tetrahydrofuran?2?carbonitrile (1191237-69-0)

Guidance literature:

With boron trichloride; In dichloromethane; at 5 ℃;

Reference yield: 75.0%

trimethylsilyl cyanide (7677-24-9) + 7-((2S,3S,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)-tetrahydrofuran-2-yl)pyrrolo[2,1-f][1,2,4]triazin-4-amine (158227-80-6) → (2R,3R,4S,5R)?2?(4?aminopyrrolo[1,2?f][1,2,4]triazin?7?yl)?3,4?dihydroxy?5?(hydroxymethyl)tetrahydrofuran?2?carbonitrile (1191237-69-0)

Guidance literature:

trimethylsilyl cyanide; 7-((2S,3S,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)-tetrahydrofuran-2-yl)pyrrolo[2,1-f][1,2,4]triazin-4-amine; With tert.-butylhydroperoxide; In dichloromethane; at 40 ℃; for 2h;

With boron trichloride; In dichloromethane; at -30 ℃; for 2h; Reagent/catalyst; Solvent; Temperature;

Reference yield: 70.0%

P-toluenesulfonyl cyanide (19158-51-1) + 7-((2S,3S,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)-tetrahydrofuran-2-yl)pyrrolo[2,1-f][1,2,4]triazin-4-amine (158227-80-6) → (2R,3R,4S,5R)?2?(4?aminopyrrolo[1,2?f][1,2,4]triazin?7?yl)?3,4?dihydroxy?5?(hydroxymethyl)tetrahydrofuran?2?carbonitrile (1191237-69-0)

Guidance literature:

P-toluenesulfonyl cyanide; 7-((2S,3S,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)-tetrahydrofuran-2-yl)pyrrolo[2,1-f][1,2,4]triazin-4-amine; With 3-chloro-benzenecarboperoxoic acid; In acetonitrile; at 60 ℃; for 2h;

With boron trichloride; In dichloromethane; acetonitrile; at 0 ℃; for 2h;

upstream raw materials:

(3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-dihydro-furan-2-one

2,3,5-tri-O-benzyl-D-ribofuranose

(3R,4R,5R)-2-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,4-bis(benzyloxy)-5-((benzyloxy) methyl)tetrahydrofuran-2-carbonitrile

(3R,4R,5R)-2-(4-aminopyrrole-[2,1-f][1,2,4]-triazin-7-yl)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-ol

Downstream raw materials:

(2S)-isopropyl 2-(((((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

(3αR,4R,6R,6αR)-4-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carbonitrile

(2S)-2-ethylbutyl 2-(((R)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate